CATCHING UP WITH RUSSELL GREGORY

Ten years since its original release as a DIY web streaming sleeper ahead of becoming a critical darling of premium cable, “High Maintenance” remains a high bar to pass in the humanity genre. The anthology series starred BEN SINCLAIR as a likable dealer who was often ensnared into the chaotic lives of his customers due to his sweet nature with feel-good or sometimes profound impact to the viewer. Over the years I found myself continually impressed with the humanity of these Brooklynites often explored so simply and delicately. Part of that humanity is the authentic way the show represents the queer community where many other fictional narratives drop the ball. 

Having crossed paths in our Brooklyn art worlds numerous times over the years, I spent some time with executive producer RUSSELL GREGORY, one of the “High Maintenance” brain trusts that developed all fifty-two episodes of the show with creators SINCLAIR and KATJA BLICHFELD. It’s here that we reflect on the show, its legacy, and—fingers crossed—its future.

M. COOPER: I guess we should have a little background on how we got to the seeding of the show. How did you first get together with Katja Blichfeld and Ben Sinclair, and what was your background before signing up to be the executive producer of High Maintenance?

RUSSEL GREGORY: Katja is really where my origin story begins with High Maintenance. Katja was a Casting Director and I was a boutique talent agent. We ended up bonding on phone calls at work but eventually took our friendship out into the real world. I’m pretty sure our first official non-work-related outing was to East Rutherford, NJ to see the Spice Girls on their reunion tour in 2007. Katja made me and my taste feel seen.

We also bonded over some of my clients at the time and Bridget Moloney was one of them. Katja accompanied me to see Bridget in Hermanas at the Fringe festival and the two of them became fast friends. I technically met Ben’s brother Dan before ever meeting Ben. Bridget and Dan were college sweethearts (now married with two children) and eventually, Bridget would leave NYC and start her life in LA with Dan. Soon after Katja was called out to LA for work and met Ben at a party. We discussed him over AOL instant messaging and on our Blackberrys a great deal before I ever met him. Katja eventually moved back to NYC and I was officially introduced to Ben in person. We hit it off right away.

MC: What was the moment where High Maintenance hatched between the three of you?

RG: After spending a decade as a talent agent in NYC, I decided to leave my job, become a talent manager and open my own production/management company, Regarding Entertainment. My dream was to cultivate a small client list and to try my hand at producing. I was a director’s assistant before becoming an agent and worked on a production of Dear World starring Sally Anne Howes and Georgia Engel. Georgia told me in her adorable voice that I reminded her of Jimmy Burrows and after that I was always seeking out how to work in television. Once we were all living in the city, Katja, Ben and I spent a lot of time together. We all had a similar sense of humor and bonded over smoking weed. It’s difficult for me to pinpoint the exact moment HM was born. I know from my POV I was constantly tossing ideas at them and practically begging them to film something with my clients. We even produced and filmed a music video for another one of my clients at the time. When they finally called me with the idea for HM, I jumped at it. It was so brilliant; short and simple but had endless possibilities for storytelling.

MC: Since its beginning as a passion project founded by the three of you, the stakes obviously escalated. From (presumable) self-funding in the very beginning to funding by Vimeo as part of their original content initiative, to HBO. Overwhelming at first with one bite at a time, or a natural transition?

RG: Katja and Ben were both such perfectionists so the stakes were always high. The bar to tell authentic stories was always up there. I would say it got more complicated with each step up. Even though we were at HBO, we were very low budget for their platform. We still couldn’t just throw money at a problem which meant we were still having to come up with creative ways of doing things to fit in budget. I believe the most helpful thing was keeping our above-the-line staff small. Only adding Willy Friedman, Gwen Bialic, and Emi Irikawa as producers along the way.

MC: During our photo shoot, you shared a few tidbits about how deeply into your personal space & life the project has gotten over the years.

One great example is that your actual apartment plays the role of the sweet Helen Hunt-obsessed Patrick’s (Michael Cyril Creighton) apartment. But that’s not all — you had a bit of art direction involved in the space in the early days. Do share.

RG: In the beginning, we filmed everything in our own spaces and our friends' spaces. My tiny apartment was on 15th street in Chelsea and became the spot where we would meet up when Katja and Ben were in the city (they were Brooklyn-based at the time).

When the story came about for the Patrick character, it felt natural it would be in my claustrophobic space. I also loved crafting (something Katja and I would do on Friday nights in NYC) and making wreaths. I had so many stocked up that Katja and Ben put them in the episode, making sure to point them out. They would later use even more of my wreaths in Patrick’s extended story for HBO. That detail meant so much to me and was another case of them making me feel seen as a creative being.

Pretty much everything on the walls in the original Helen episode was art that I had made. When the character came back again later in HBO episodes, obviously our crew brought in some professional work, but there’s still a lot of my art in there. My landlord at the time was very kind to let us film in my tiny apartment and my neighbors were also very kind to let us film in the claustrophobic hallways of the building.

MC: I think I read somewhere that you went from a five person crew in the original web series Patrick story, but that must have been a sweet memory by the time you had the whole HBO crew in there. The genuine settings became a staple that the show was known for, but what was the location scouting process like from the humble beginnings to the network broadcast?

RG: We performed almost every crew position ourselves in the early days. Our friends would also volunteer their time to help us. We would film for just a day or two and it was usually over holidays and weekends because we had full time jobs during the week. Locations were very difficult to come by in the early days. I remember during the Qasim episode Katja and Ben wanted the character to take a nap in a tanning bed. I went door to door at all the tanning salons in my Chelsea neighborhood and eventually found one but what a stressful job. We were very lucky to have Julie Sage doing locations on our HBO episodes. She understood the tone of the show so well and did a masterful job in finding spots that kept the spirit of the show but also worked in our budget. She was put in such a difficult position because when people would hear HBO production they would think we had a pocketbook full of money but we truly didn’t. We were low budget for an HBO show (but we stretched that budget as far as we could!)

MC: Have you ever heard from Helen Hunt about your paintings and the adornment that HM has shown her?

RG: Every year while doing press in LA, we would go to the HBO offices to speak to Casey Bloys and find out if we were getting picked up for another season. That first year, while we were waiting in the lobby, Helen Hunt walked in. It was such a fantastic omen. I don’t remember the exact exchange because I pretty much blacked out with joy, but she was so kind and seemed to enjoy how we displayed her on the show. I believe Michael Cyril Creighton (who played Patrick) also had exchanges with her over social media and he said feedback was always positive.

MC: In “Olivia”, S1 E4 of the Vimeo series, you introduced us to one of the great modern comedy pairings - Helené Yorke as Lainey & Max Jenkins as, well, Max. (Read our interview with Max Jenkins here.) Describe the humble origin of bringing these two great actors in and how their characters came to be to the place they evolved to by the time we get to their final encounter in the series.

RG: Heléne was a long-time management client of mine (and I was her agent prior to that) so I was constantly pushing her for a story on HM. Katja had been working on 30 Rock (eventually winning an Emmy for that work) and had cast both Heléne and Max separately on that show. After that, Katja had always wanted to put the two of them together and had a sixth sense that they would make a good duo. When Katja and Ben were coming up with webisode ideas, Katja pitched that they write an episode for Heléne and Max. That’s how so many of those early episodes came about – the actor ideas often came first and a story would get written for them. Heléne and Max had never met before but when they did, it was instant chemistry. 

They’re still very good friends today! That was an episode that was so natural and funny and we were lucky they continued to come back multiple times. I love Heléne’s appearance in the Rachel Comey showroom in the Rachel episode and Max popping up in the Matilda episode. We would later use them to begin the HBO run of the show and also in the finale season.

MC: For Season Two, as part of the team you assembled a hell of a roster of new writers & directors. What was it like to begin moving away from the previous episodes having been under the sole authorship of Ben & Katja and discover these new voices that had so much to say about these beloved characters? 

RG: This was such an amazing experience. Being able to employ so many artists and creatives will forever be a special moment in my life. Katja and Ben knew of so many people and had such great taste. They were committed not just to have seasoned writers, but also newcomers and storytellers, in order to keep the show fresh. Shaka King (during his interview at a coffee shop in Brooklyn, his mother happened to walk by and we were lucky enough to meet her and see him interact with her and we knew he was such the right fit for the show), Eliza Hittman, Silas Howard, Hannah Bos and Paul Thureen, Isaac Oliver, Mel Shimkovitz, Zach Shamberg, Gary Richardson, Mitra Jouhari, Rebecca Drysdale and so many others. I could go on and on. I will be forever grateful for all of these people for sharing their stories, talent and creativity with us.

MC: One of my favorite things that I’ve mentioned to you is the cameos that many of the characters have within the storylines of others, or sometimes even just popping up in the background. Do you have a personal favorite of these?

RG: This was my favorite thing, too. I loved when they would bring characters back. Again, I’ll try to name a few but there really are so many talented people with complete stories in our series. Our fantastic casting director Andrew Femenella introduced us to Skittlez Ortiz. Skittlez always made us smile. We loved that character and had him pop up a few times. Also Pinky (Jamie Simon) as a street performer was always a treat. Her telling the Guy’s niece that she “loved her skinsuit” in the Matilda episode also became a catchphrase for the three of us. Max Wittert and Julio Torres had an iconic cameo (“The chair is mi-ine”) and Max came back for our Breathwork episode. We brought back A TON of people in that episode. Lots of characters from our swingers group (Mussebat episode) - Amy Ryan, Dan Steven, Katja Blichfeld, Cathay Trein. Jawnee Conroy who was a scammer in the Matilda episode was also seen running crafty in Breathwork. People from the pro-feminist meet up like Jo Firestone (as Amy Ryan’s assistant). Jo was also Bridget Moloney’s assistant in the Tick episode from season one. The Breathwork episode is just littered with inside jokes and people we loved. Azar Kahn came back many times, eventually playing a Janky Clown (which is our production entity name). Evan the asexual magician (Avery Monsen) comes back a lot and is in one of my favorite episodes about an intimacy coordinator. Dan Stevens came back a few times and was always a joy to have around. I could go on forever about the actors we worked with. They were all so much fun and so willing to play with us.

MC: On a similar note, do you have any favorite characters across the 52 episodes whose arcs you were invested in from their intros to their conclusions?

RG: I love so many of our characters and so many of them got complete lives on our show. It’s hard to pick a favorite. I guess I have to say that the completion of Max’s storyline brought me joy. I love the scene with Max and Lainey in the car. The reveal that he’s now Hari Krishna is perfect. The fact that he’s dancing with such joy with his new Hari Krishna family after being tortured and beaten down by his frenemy Lainey, always makes me tear up. I’m pretty sure I cried that whole night. Max is so happy and it always warms my heart to know he survived that toxic relationship.

MC: You made your acting debut in the Season 4 episode “Backflash” as an upbeat food blogger dealing with a bit of grumpiness from his partner. How did you end up cast in the role, and what was it like being on the other side of the camera?

RG: That was completely unplanned. The script was originally written for John Early and Harvey Firestein but because of our tight schedule and actor availability, we just couldn't make it work. Casting went out to other people after that but again, we had such a tight schedule, we were having trouble lining anyone up. We were set to start on a Monday and the Friday prior, I asked Katja and Ben if they had any other backup ideas and Katja said “yes, you.” 

The character I played was very loosely based on my uncle who made some amateur cooking videos in his apartment and posted them on Facebook. One in particular always made us crack up. So it felt natural that I would be the backup choice. Also, it felt like the web series again with one of us stepping in as an actor. The moment where my character says “See you round the campus” and The Guy in a ski mask says “What campus?”, was pulled directly from my uncle’s video and really made the whole thing come full circle. It truly makes me cry to think of it. We laughed so hard so many times and “what campus” became another staple catch phrase with our HM family.

MC: As a team, how did you begin to craft the ending to the show? The speculation my friends & I had the entire run was that we’d know it was the end when we learn The Guy’s name. Was that always the plan?

RG: We tried to end every HBO season like it was the last. We never knew if we would be picked up again so we tried to have a satisfying ending to each HBO season. In the first web series script, The Guy had a name and it was Rufus. They ended up omitting that detail out so when it was time for his niece to talk to him, the name Rufus came back into play.

MC: And what do you think happened to Rufus?

RG: It’s hard to say and I’m sure we all have our thoughts but if you watch the final episode, with all the flight attendants in their crash pad, it seems as though Katja, Ben and our writers sort of predicted the Covid lockdown. There’s even one flight attendant wearing a mask. So I think that Rufus, wisely, went to New Zealand (as they were less touched by Covid in the early days). I would also guess he would have disliked the state of America after that and just stayed in NZ. Opened a nursery or something. Also an interesting detail from our first episode STEVIE, the Guy clocks Quinn’s medications and basically gets her to try weed again and lay off the Klonopin, etc. Then in the final episode, The Guy’s niece gives him Klonopin to help him stay calm on the long flight. A full circle detail.

MC: There always seems to be talk of High Maintenance returning. I keep my hopes up, personally. What do you think, though?

RG: Never say never but it doesn’t seem to be anyone’s focus these days. It feels to me like a very complete journey and is satisfying so I’m not sure any of us want to mess that up by trying to force something new. It had it’s time and we were very lucky and I hope one day it might have a rewatch renaissance but as far as continuing the Guy’s story, I can’t see it.

MC: Do you have a personal favorite episode or storyline from the 52 episode run and if so, which?

RG: This is a tough question because I love so many storylines and moments from the show. The Brad Pitts episode will always be a favorite because we used our mothers’ quirks as inspirations for the story. I love that we were able to bring back the incredible Birgit Huppuch for later episodes and give her a complete story. Her character, Ellen, will always have a special place in my heart. The scene where she dips her date’s testicles into milk will always make me laugh out loud.

MC: And finally, what have you moved on to since the closing of High Maintenance?

RG: I’m still working very closely with many of the HM family we formed. I was recently at our sound designer’s wedding and I’m the godfather to our producer/DP’s child. I’ve driven both Heléne Yorke and producer Emi Irikawa home from the hospital after giving birth to their children. The show has given me relationships and experiences that I would’ve never had otherwise. After producing High Maintenance, something so original and special and personal, it’s been hard to be interested in other producing projects but I’m still managing talent and there will be some pitching of new projects in 2024.